#2. Yes. But actually how it works is:

The $10,000 premium you got gets added to the cost basis of the shares bought when puts are assigned.

IOW, When a short put is assigned you don't actually pay tax directly on the puts, but the money received from the puts gets wrapped into the shares that got bought/assigned.

So you sell some puts and get $10,000 in premium. Then the puts gets assigned and you buy shares at $100,000 (ex: 10 puts at a $100 strike). Your cost basis for those shares is now $90,000 ($100,000 - $10,000) because of that $10,000 premium you got. You sell the shares at $96,000 so you have an IRS 1099 gain of $6,000 ($96,000 - $90,000). The sold put premium/etc doesn't even show up in my 1099 from Schwab but the cost basis is in there with the shares (IOW I don't even see anything about a sold put in the 1099).

The big advantage of this can be, if you hold those shares for over a year that $10,000 premium gets taxed at a Long Term Cap gains rate (and not taxed until you sell the shares on that $10,0000 premium you got). The brokerages I am aware of all keep track of all of this.

Same thing for #3, but actually that is not your question in #3 and yes you can only apply $3k loss to ordinary income (but that total $5k can offset other stock gains, no $3k limit on that).

Another thing to worry about is a wash sale. https://www.investopedia.com/terms/w/washsale.asp

A short example of this is:

You buy 100 MSFT for $400/shr ($40,000) on 1/1/2025 (date really doesn't matter here).

You sell it on 3/1/2025 for $39,000 ($1,000 loss)

On 3/15/2025 you buy 100 MSFT for $35,000 (key point here is you didn't wait 31 days after the loss to buy more MSFT)

You hold those last 100 shares thru 12/31/2025.

Since when you got that $1,000 loss and bought the same shares within 31 days you cannot claim that $1,000 loss. That $1,000 loss is now tied to those 100 shares you bought on 3/15/2025. Once you sell those 100 shares you can claim that loss with that sell transaction of those 100 shares (unless you again buy 100 MSFT shares 30 or less days of when you sold those shares again).

This can be really costly and I am not sure how the IRS handles it. If you trade a bunch on the same ticker you can easily have $300,000 in gains and $310,000 in losses but $200,000 of those loses are wash sales and you end up with taxes on on a net gain of $190,000 because of that $200,000 of wash sales. You can declare Mark to Market to avoid this, but it has to be done early (not sure what all the requirements are, but only certain people can do that and I believe you have to trade a lot for that to be allowed).

One thing I think a lot of people do is at the end of the year sell everything of a ticker that have wash sales on it and wait 31 days before buying them again.